Hydrogen Peroxide → HCID 53840815, compound

Participants

Reaction Steps

To a solution of Compound (XIV) (1.80 g; 2.29 mmoles) in tetrahydrofuran (25 mL), cooled at 0° C., was added a 1.0M solution of borane-dimethylsulfide complex in tetrahydrofuran (1.5 mL). The reaction was warmed to room temperature and kept for 20 hours. After cooling to 0° C., 3N NaOH solution (15 mL) and 30W% hydrogen peroxide (0.5 mL) were added, and the suspension was heated under reflux for 1 hour. Upon cooling to room temperature, the suspension was mixed with water (10 mL) and extracted with ether (2×40 mL). The combined organic solution was washed with saturated sodium chloride solution, dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the crude residual oil was purified via flash chromatography (silica gel; 1:2 ethyl acetate:hexane) to yield the primary alcohol, 1-[3,4,5-tris(phenylmethoxy)-6[(phenylmethoxy) methyl]-1-(phenylmethyl)-2-piperidinyl]-1,4-butanediol 1-benzoate (XV), as a clear, colorless oil (1.05 g; 56.9%) and the 1,4-diol, 1-[3,4,5-tris (phenylmethoxy)-6-[(phenylmethoxy)methyl]-1-(phenylmethyl) -2-piperidinyl]-1,4-butanediol (XVIII), as a yellow oil (0.41 g; 24.9%). Compound (XV): IR(neat) 1720 cm-1 (C=0); MS (FAB-MNBA) 806 (MH+), 788 (MH+H2O); 1H nmr (CDCl3) δ 1.5-1.9 (m, 2H), 2.8 (t, 1H), 3.4 (t, 2H), 3.5 (m, 1H), 3.7-4.2 (m, 7H), 4.3-4.4 (m, 1H), 4.4 (s, 2H), 4.5-4.9 (m, 7H), 5.4-5.5 (m, 1H), 7.0-7.4 (m, 27H), 7.5 (m, 1H), 8.1 (m, 2H).

Provenance & Evidence